Boron-selective biaryl coupling approach to versatile dibenzoxaborins and application to concise synthesis of defucogilvocarcin M

Yuto Sumida; Ryu Harada; Tomoe Kato-Sumida; Kohei Johmoto; Hidehiro Uekusa; Takamitsu Hosoya

doi:10.1021/ol5031734

Boron-selective biaryl coupling approach to versatile dibenzoxaborins and application to concise synthesis of defucogilvocarcin M

Org Lett. 2014 Dec 5;16(23):6240-3. doi: 10.1021/ol5031734. Epub 2014 Nov 24.

Authors

Yuto Sumida¹, Ryu Harada¹, Tomoe Kato-Sumida¹, Kohei Johmoto², Hidehiro Uekusa², Takamitsu Hosoya¹

Affiliations

¹ †Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
² ‡Department of Chemistry and Materials Science, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8551, Japan.

PMID: 25418801
DOI: 10.1021/ol5031734

Abstract

An efficient synthetic method for versatile dibenzoxaborins based on boron-selective Suzuki-Miyaura cross-coupling between o-borylphenols and aryl halides or triflates bearing a 1,8-diaminonaphthalene-protected o-boryl group is reported. A short synthesis of defucogilvocarcin M was achieved using the proposed method in combination with several other boron-mediated transformations.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

2-Naphthylamine / analogs & derivatives
2-Naphthylamine / chemistry
Benzopyrans / chemical synthesis
Benzopyrans / chemistry
Boron / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Molecular Structure

Substances

Benzopyrans
defucogilvocarcin M
2-Naphthylamine
1,8-diaminonaphthalene
Boron